This invention relates to novel 1-dimethylcarbamoyl-3-t-butyl-5-(carboalkoxy)alkylthio-1H-1,2,4-triazoles which are useful as insecticides, molluscicides and plant growth regulating agents, compositions containing those compounds and methods of use.
The search for compounds which have a combination of excellent activity and essentially no undesired toxicity is a continuing one due to recognition of the possible toxicity to animals and humans of many known pesticides.
Certain 1,2,4-triazoles have been disclosed as having pesticidal activity.
U.S. Pat. No. 3,308,131 describes a group of 1,2,4-triazoles having the general formula ##STR1## and ##STR2## where X is oxygen or sulfur, R.sup.5 and R.sup.6 are aliphatic groups containing up to 14 carbons and which may be joined to form a heterocyclic ring with the carbamoyl nitrogen atom and R.sup.7 and R.sup.8, which together contain up to 14 carbon atoms, are free from aliphatic unsaturation and are selected from hydrogen, halogen, sulfonyl, mercapto, cyano, hydrocarbyl, halohydrocarbyl, nitrohydrocarbyl, hydroxycarbyloxycarbonylhydrocarbyl, hydrocarbylsulfonyl, hydrocarbylmercapto, nitrohydrocarbylmercapto, halohydrocarbylmercapto, aminohydrocarbylmercapto and hydrocarbyloxyhydrocarbyl. These compounds are said to be useful as insecticides, in dyeing textiles and as analgesics.
U.S. Pat. No. 4,291,043 describes 1-N,N-dimethylcarbamoyl-3(5)-alkyl-5(3)-alkylthioalkylthio-1,2,4-triazoles having insecticidal activity. The 3(5) substituents include i-propyl, s-butyl, t-butyl or optionally methyl-substituted cyclopropyl and a group having the formula EQU --S--CH(R')--(CH.sub.2).sub.n --S--R"
where R' is H or methyl, R" is lower (C.sub.1 -C.sub.4)alkyl and n is zero or 1.
U.S. Pat. No. 3,973,028 describes 1-dimethylcarbamoyl-3-branched alkyl-1,2,4-triazol-5-yl-(N-substituted)sulfonamides having insecticidal activity.
U.S. Pat. No. 4,054,664 describes 1(2)-(N,N-disubstituted carbamoyl)-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3(5) substituents include isopropyl), s-butyl, t-butyl, and S--R where R is methyl, ethyl, propyl, vinyl, prop-2-ynyl, but-2-enyl or 2-haloalkyl.
U.S. Pat. No. 4,160,839 discloes 1-N,N-dimethylcarbamoyl-3,5-substituted-1,2,4-triazoles having insecticidal activity. The 3-substituents include t-butyl, propyl, cyclopropyl, isopropyl or 1-methylpropyl. The 5-substituents include S--R where R is 2-propynyl, allyl, 2-bromoallyl, 2-chloroallyl, 2-methylallyl, 1-methylallyl or 2,3,3-trichloroallyl.
U.S. Pat. No. 4,220,790 discloses 1-N,N-dimethylcarbamoyl-3-tert-butyl-5-methylthio-1,2,4-triazole having insecticidal activity.
The present invention discloses 1-dimethylcarbamoyl-3-t-butyl-5-(carboalkoxy)-alkylthio-1H-1,2,4-triazoles . These compounds are distinguished primarily by their novel 5-position substituents.
Compounds of the present invention are also distinguished by their excellent insecticidal activity against sucking insects such as those of the order Homoptera and especially those of the family Aphididae; that is, these compounds are highly selective. More particularly, these compounds possess very good contact action and are plant systemic through both foliar and root absorption. Further, compounds of the present invention exhibit very good residual properties through both foliar and root absorption and transport.
Certain compounds of the present invention are also distinguished by their plant growth regulator effect. Further, certain compounds of the present invention are distinguished by their molluscicidal activity.
Accordingly, compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants and ornamentals, especially in crops of fruits, vegetables and cereals. Certain compounds are suitable as plant growth regulating agents and certain compounds are suitable for controlling molluscs.
It is therefore an objective of the present invention to provide novel compounds, and compositions containing said compounds, which possess one or more of insecticidal, plant growth regulatory and molluscicidal activity. It is a further object of this invention to provide methods for controlling insects, regulating plant growth and/or controlling molluscs using the novel compounds.